9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione → 9-hydroxy-4-(3-hydroxy-4-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11016Notes

Reaction equation

HRID 11016 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:12]2[NH:11][C:10]3[CH:9]=[C:8](I)[C:7]4[C:16](=[O:20])[NH:17][C:18](=[O:19])[C:6]=4[C:5]=3[C:4]=2[CH:3]=1.[OH:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][C:27]=1[O:28][CH3:29]>>[OH:1][C:2]1[CH:14]=[CH:13][C:12]2[NH:11][C:10]3[CH:9]=[C:8]([C:24]4[CH:25]=[CH:26][C:27]([O:28][CH3:29])=[C:22]([OH:21])[CH:23]=4)[C:7]4[C:16](=[O:20])[NH:17][C:18](=[O:19])[C:6]=4[C:5]=3[C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 118428349-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneHCID 21980666(3-Hydroxy-4-methoxyphenyl)boronic acid

Product 1

HCID 219803389-hydroxy-4-(3-hydroxy-4-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneYield 51%

Procedure

The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 3-hydroxy-4-methoxybenzeneboronic acid according to the procedure described in example 8 gave 9-hydroxy-4-(3-hydroxy-4-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (10) (1, Ar=3-hydroxy-4-methoxyphenyl) (51%), mp 265° C. (dec). 1H NMR δ [(CD3)2SO] 11.67 (s, 1H), 10.96 (s, 1H), 9.22 (s, 1H), 9.15 (s, 1H), 8.33 (d, J=2.4 Hz, 1H), 7.57 (s, 1H), 7.41 (d, J=8.7 Hz, 1H), 7.22 (d, J=2.0 Hz, 1H), 7.06–6.99 (m, 2H), 6.85 (d, J=8.1 Hz, 1H), 3.81 (s, 3H). EIMS found M+: 374.0900. C21H14N2O5 requires 374,0903.

Sources & evidence

ORD record
ord-a6f215557f6b417b8f4a6b2176b51e11
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

Loading…